Visible-Light-Catalyzed Formal [3+2] Annulation-Aromatization of Amidines with Isoquinolinium N-Ylides: Access to Imidazo[2,1-a]isoquinolines

被引：6

作者：

Zheng, Lvyin ^{[1
]}

Zou, Xiaoying ^{[1
]}

Yang, Xiaojuan ^{[1
]}

Deng, Lei ^{[1
]}

Guo, Wei ^{[1
]}

机构：

[1] Gannan Normal Univ, Key Lab Organo Pharmaceut Chem Jiangxi Prov, Ganzhou 341000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2023年 / 365卷 / 21期

基金：

中国国家自然科学基金;

关键词：

visible light catalysis; 3+2] annulation-aromatization; imidazo[2,1-a]isoquinolines; amidines; isoquinolinium N-ylides; C-H ACTIVATION; ONE-POT SYNTHESIS; METAL-FREE; CYCLOADDITION REACTION; OXIDATIVE CYCLIZATION; TANDEM ANNULATION; BOND FORMATION; DERIVATIVES; STRATEGY; PYRIMIDINES;

D O I：

10.1002/adsc.202300926

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A visible-light-catalyzed formal [3+2] annulation-aromatization reaction for the synthesis of various substituted imidazo[2,1-a]isoquinolines from amidines with stabilized isoquinolinium N-ylides in the presence of bases is developed. The procedure reported here involves a direct C-H activation and the formation of C-C/C-N bonds in one-pot. The reaction mechanism is probed by radical-trapping experiment, fluorescence quenching, and light on/off experiments. The late-stage modification experiments provide the potential applications in the field of organic and medicinal chemistry for chemists.

引用

页码：3629 / 3636

页数：8

共 95 条

[51] Nickel-catalyzed oxidative C-H/N-H annulation of N-heteroaromatic compounds with alkynes [J].

Obata, Atsushi ;

Sasagawa, Akane ;

Yamazaki, Ken ;

Ano, Yusuke ;

Chatani, Naoto .

CHEMICAL SCIENCE, 2019, 10 (11) :3242-3248

[52] One-pot concise syntheses of benzimidazo[2,1-a]isoquinolines by a microwave-accelerated tandem process [J].

Okamoto, Noriko ;

Sakurai, Keisuke ;

Ishikura, Minoru ;

Takeda, Kei ;

Yanada, Reiko .

TETRAHEDRON LETTERS, 2009, 50 (28) :4167-4169

[53] CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of Iodoisoquinoline-Fused Benzimidazoles [J].

Ouyang, Huang-Che ;

Tang, Ri-Yuan ;

Zhong, Ping ;

Zhang, Xing-Guo ;

Li, Jin-Heng .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :223-228

[54] Synthesis of Imidazopyridines via Copper-Catalyzed, Formal Aza-[3+2] Cycloaddition Reaction of Pyridine Derivatives with α-Diazo Oxime Ethers [J].

Park, Sangjune ;

Kim, Hyunseok ;

Son, Jeong-Yu ;

Um, Kyusik ;

Lee, Sooho ;

Baek, Yonghyeon ;

Seo, Boram ;

Lee, Phil Ho .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (19) :10209-10218

[55] Nucleophilic Addition of Benzimidazoles to Alkynyl Bromides/Palladium-Catalyzed Intramolecular C-H Vinylation: Synthesis of Benzo[4,5]imidazo[2,1-a]isoquinolines [J].

Peng, Jinsong ;

Shang, Guoning ;

Chen, Chunxia ;

Miao, Zhongshuo ;

Li, Bin .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03) :1242-1248

[56] Electrocatalytic Tandem Synthesis of 1,3-Disubstituted Imidazo[1,5-a]quinolines via Sequential Dual Oxidative C(sp3)-H Amination in Aqueous Medium [J].

Qian, Peng ;

Yan, Zicong ;

Zhou, Zhenghong ;

Hu, Kangfei ;

Wang, Jiawei ;

Li, Zhibin ;

Zha, Zhenggen ;

Wang, Zhiyong .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (06) :3148-3157

[57] Synthesis of imidazo and benzimidazo[2,1-a]isoquinolines by rhodium-catalyzed intramolecular double C-H bond activation [J].

Reddy, Vutukuri Prakash ;

Iwasaki, Takanori ;

Kambe, Nobuaki .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (14) :2249-2253

[58] Synthesis of Disubstituted 3-Phenylimidazo[1,2-a]pyridines via a 2-Aminopyridine/CBrCl3 α-Bromination Shuttle [J].

Roslan, Irwan Iskandar ;

Ng, Kian-Hong ;

Wu, Ji'-En ;

Chuah, Gaik-Khuan ;

Jaenicke, Stephan .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :9167-9174

[59] 2-Aminopyridines as an α-Bromination Shuttle in a Transition Metal-Free One-Pot Synthesis of Imidazo[1,2-a]pyridines [J].

Roslan, Irwan Iskandar ;

Ng, Kian-Hong ;

Chuah, Gaik-Khuan ;

Jaenicke, Stephan .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (03) :364-369

[60] AgI-Catalyzed Cascade Strategy: Regioselective Access to Diversely Substituted Fused Benzimidazo[2,1-a]isoquinolines, Naphthyridines, Thienopyridines, and Quinoxalines in Water [J].

Rustagi, Vineeta ;

Tiwari, Rakesh ;

Verma, Akhilesh Kumar .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (24) :4590-4602

← 1 2 3 4 5 6 7 8 9 10 →